Therapeutically active amidines



Patented Sept. 27, 1938 The following the parts being Karl Miesch Basel, Switzerland N Drawing.

examples illustrate the by weight- Example 1 phenoxyacetonit Application In Switzerland, June 21, 1935 The a-phenoxy-n-buteny1-di-n-buty1ami- Claims.

invention phenoxacetimidoether-hydrorile, alcohol and hydrogen chloride) are shaken with a ordinary temperature.

solution is allowed to stand for some evaporated.

CoHa-O-CHzC separates in the form powder, melting at 201 ble in water. Instead of tion may also for example of ,B-phenylethylamine in time and PhenoXyethenyl-p-phenylethylamidine-hydrochloride of the formula of a colourless crystalline 203 C. and freely soluwith S-phenyIethyIamine the reacbe carried out in similar manner With piperidine or piperidine-ethylamine.

Example 2 amine. After 15 hours the clear solutio orated and th e residue recrystallized phenylethyl-N-methylamine,

are mixed with s of di-n-butyl- 1']. 1S evapfrom aceof Chemical r, Riehen, near Basel, and Ernst Urech, Basel, Switzerland, firm of Society assignors to the Industry in Basle,

June 15, 1936, Serial tone. dine-hydrochloride thus obtained and having the formula 1 NH-HVOI CuH- O- 0112- CH3- CH2' C/ is a colorless crystalline powder melting at 117- Instead of di-n-butylamine there may also be used another amine, such as for example diethylamine, methyl-ethyl-amine, benzylamine or diethylamino-ethylamine.

Instead of oc-PhBHOXY-Il-blltYIOl'litIilG one may start for instance from u-phenoxy-n-butyronitrile of the formula CoHs-O-(FH-CN CgHt What we claim is:- 1. Phenyloxy-alkylene-amidines cals being of the lower aliphatic series.

2. The phenoxy-ethylene-;3-phenylethyl-amidine of the, formula /NH C H2- 0112- C 0H5 OaHa-O-CHaC NH forming a colorless crystalline hydrochloride, melting at 201-203 ,C., which is freely soluble in Water.

3. The a-phenoxy-n-butylene-di-n-butylamidine of the formula NH CaH5-O-CHz-CHz-CHz-C N(G Ha)2 forming a colorless crystalline hydrochloride melting at 117-118 C.

KARL MIESCHER. ERNST URECH. 

